Article updated at 3:13 p.m. EDT on May 6, 2013 to correct reference to Lamborghini paddles being used for steering. The paddles are used for shifting.

Last fall, I had the opportunity to drive a Lamborghini at a corporate event that I attended in Monterey, Calif. This was a very cool experience since I have never driven such an expensive ($200,000-plus) car, let alone a serious racing car on a racecourse. When I was being prepped to drive it, the professional driver that was to be in the car with me went through the cockpit controls and showed me how they all worked. The dashboard controls looked like they were from an airplane, given the number of dials and complex features.

The instructor pointed out that while the car had a steering wheel, it also had the racing paddles used for shifting gears, which made steering the car easier and smoother when going fast on a racetrack. These are amazingly sensitive paddles that make controlling the car easier at fast speeds with curves; they’re not for the untrained or faint of heart. When he was showing me these paddles, I became very concerned. I thought he was trying to teach me to use them too quickly before we were to take off. Thankfully, he said the paddles would be disengaged, and I would use the steering wheel for our drive. He also disabled a lot of other features a true race-car driver would use. As a result, I was basically sitting in a normal car with a normal steering wheel, brake, accelerator and speed gauges.

The fact that I was going to get the car to 100-plus miles an hour on the straightaway still freaked me out, but the knowledge that I knew how to drive a normal car, even if this version was a race car, was ultimately comforting. The drive was truly exciting, but as I reflected on it, this race car was pretty much a normal, albeit highly expensive and very souped-up car. And because I knew how to drive a car, I was easily able to jump in and take off with very little instruction.

When Apple introduced the Mac in 1984, millions of PC users had learned to use a computer via DOS commands. Apple’s graphical user interface was revolutionary for DOS users, and very few PC users made the jump to Mac in its early days. However, it struck a nerve with graphics professionals and desktop-publishing professionals. Because of what it could do for them, they were willing to accept the leaning curve in order to master the newfangled interface Apple gave them on the Mac. For others, it was their first computer, and so they learned to use a computer with the Mac’s user interface from scratch.

In 1985, Microsoft realized that the Mac’s graphical user interface might be an important upgrade in user-interface designs, and so the company created the first version of Windows, which eventually became known as Windows 1.0. In 1987, Microsoft introduced Windows 2.0. However, these early versions were considered shells that ran on top of DOS, and it was not until Windows 3.0 was introduced in 1990 that Microsoft added support for virtual memory, which allowed sharing of DOS apps with Windows apps. At that point, the move to Windows began to pick up steam among even die-hard DOS users. But for those five years, when a PC booted up, it booted to DOS and gave users a togglelike approach to switch between DOS and Windows at will.

With the introduction of Windows 95 in 1995, DOS was pretty much history. It is important to note here that the actual transition from DOS as a mainstream interface to Windows took at least five to seven years to accomplish.

While I was entrenched in DOS in those early days of PCs, I jumped to the Mac for one major reason. As a market-research house, we published dozens of reports a year back then. At that time, we had to farm out the final layout and actual printing to a graphics-editing house, and then finally to an actual printing service. When the Mac introduced us to desktop publishing, pretty much all companies that did a lot of publishing quickly jumped to the Mac because it cut costs dramatically and gave us full control over much of the publishing process. Had desktop publishing been available on a DOS machine back then, I probably would have stayed with DOS PCs. However, desktop publishing did not come to the PCs until Windows was in full swing in the early 1990s.

With the introduction of the iPhone and the iPad, Apple again pushed the envelope of user-interface design by making touch an integral part the iPhone and iPad user experience. Once it became clear that touch was the next evolution in user interfaces, Microsoft began to diligently develop touch-based user interfaces of its own. These were first implemented on the Windows Phone line and last fall made their way to PC and tablet products. From a strategic standpoint, Microsoft clearly felt left behind by Apple’s success in touch-based smartphones and tablets, and I think Microsoft’s accelerated move to put touch on Windows PCs was its way of one-upping Apple.

However, Microsoft’s strategic blunder came when the lessons it learned from the past were not carried forth to the launch of the Windows 8 operating system. From the introduction of the IBM PC in 1981, people became conditioned to use DOS as the user interface. Microsoft took about five to seven years to help its customers completely migrate from DOS to Windows. Part of this was a tech problem since Windows 1.0 and Windows 2.0 were just shells; it took Microsoft a long time to develop the code with which Windows was the primary operating system, and DOS was the fallback operating system with full backward compatibility between the two.

But this time around, Microsoft basically threw users of Windows 8 a brand new touch interface and took away a key part of every Windows user’s navigational tools: the Start Button. Microsoft forced people to boot into Windows 8’s touch-friendly interface, but left out the way people have been used to launching into the desktop for the past 20-plus years. It would be like if the race-car instructor were to have taken the steering wheel out of the Lamborghini and told me to use the paddles to shift. Sure, over time I could learn to use the paddles, but to get going now, I need the steering wheel.

I suspect many people who get new PCs with Windows 8 on them feel similar frustrations. After 20 years of the Start Button (steering wheel) it’s gone, and now they have paddles (touch) to work with. Microsoft could have done a lot to make this transition smoother, such as by putting boot-to-touch only on touch-based PCs and then having a toggle button to go from the touch interface to the traditional Windows interface. Or work with the track-pad vendors to map to touch while still keeping the Start Button in place as an option.

This strategic blunder has kept millions of people from jumping on the Windows 8 bandwagon. We are now hearing rumors that the next release of Windows, code-named Windows Blue, will have the Start Button on it. If that is true, it might help get more people to buy Windows 8. However, Microsoft’s blunder has cost it and its partners dearly over the past nine months.

Could Windows 8 eventually catch on? Perhaps it can over time. But if Microsoft does not do a better job of easing people into Windows 8, it could be quite a while before current Windows users adopt this new operating system that radically changes the way they interact with PCs and laptops.

Bajarin is the president of Creative Strategies Inc., a technology-industry analysis and market-intelligence firm in Silicon Valley. He contributes to Big Picture, an opinion column that appears every Monday on TIME Tech.